—Disulfonimide Design Aids Organocatalysis “Chemists in Germany have designed a binaphthyl-based disulfonimide as a new motif in asymmetric organocatalysis” Chemists in Germany have designed a binaphthyl-based disulfonimide as a new motif in asymmetric organocatalysis (Angew. Chem. Int. Ed., DOI: anie.200901768). The catalyst created by Benjamin List and coworkers of the Max Planck Institute for Coal Research helps resolve some challenges for enantioselective organocatalysis, namely identifying new active functional groups, achieving higher catalyst turnover rates, and activating aldehydes. The team zeroed in on the binaphthyl design commonly used for chiral catalysts and selected the disulfonimide as a mimic for triflic-based compounds such as (F3CSO2)2NSi(CH3)3 that are powerful but nonselective acid catalysts.
by Stephen K. Ritter | May 25, 2009
—Organocatalysis Expands “Synthesis: Method directly yields β-functionalized aldehydes” A new reaction expands the use of organocatalysis to the production, in a single step, of β-functionalized aldehydes, an important class of compounds that normally cannot be made so quickly and easily. By providing a new catalytic route to these compounds, the work adds to the armamentarium of synthetic organic chemistry.
by Stu Borman | March 03, 2011
—Pioneers of asymmetric organocatalysis win 2021 Nobel Prize in Chemistry “Benjamin List and David W. C. MacMillan take home the prize for revolutionizing chiral organic synthesis with small-molecule catalysts” The 2021 Nobel Prize in Chemistry has gone to Benjamin List of the Max Planck Institute for Kohlenforschung and David W.
by Leigh Krietsch Boerner | October 09, 2021
—Gel Formation Induces Organocatalysis “An L-proline-based compound that forms supramolecular gels also acts as an organocatalyst for the Henry reaction” An L-proline construct that forms supramolecular gels can also act as an organocatalyst, reports Francisco Rodríguez-Llansola, Beatriu Escuder, and Juan F.
by Jyllian N. Kemsley | June 08, 2009
—Designer Surfactant For Organocatalysis “An amphiphilic molecule bearing a proline group provides a micellar system for running metal-free organic reactions in water” A micelle-forming molecule that functions as a solvent, surfactant, and organocatalyst rolled into one provides a “green” platform for carrying out organic reactions in water, according to Bruce H.
by Stephen K. Ritter | January 09, 2012
But “used creatively, organocatalysis is much more than a replacement technology for metal catalysis,” according to David W. C. MacMillan, a chemistry professor at California Institute of Technology and a major proponent of organocatalysis. The greater excitement lies in catalysis of reactions that were not even thought possible, he adds.
by A. MAUREEN ROUHI, C&EN WASHINGTON | September 06, 2004
—Functionalized Biaryls By Organocatalysis “Organic Synthesis: Organic acid-catalyzed reaction yields compounds that are promising as ligands and catalysts” Biaryl compounds with a 1,1´ linkage are popular as ligands and catalysts for preparing chiral drug molecules. The 1,1´-biaryl structure also shows up in numerous natural products.
by Bethany Halford | December 07, 2015
—Chemistry On Cloth “Catalysis: Modified textiles offer new method for organocatalysis” Organocatalysts have become fashionable in chemistry circles during the past decade. Now, chemists are taking a cue from fashion by immobilizing these small, nonmetallic organic catalysts onto fabric (Science 2013, DOI: 10.1126/science.1242196). The new organotextile catalysts offer a general, inexpensive, and practical approach to solid-supported organocatalysis, which aids catalyst recycling and could find use in the manufacture of pharmaceuticals and fine chemicals. “The difficulty with any catalyst that is not supported on a heterogeneous material is that the recovery from homogenous phase requires an additional operation,” explains Benjamin List, of Germany’s Max Planck Institute for Coal Research, who spearheaded the organotextile research.
by Bethany Halford | September 16, 2013